Record Information
Version1.0
Creation date2011-09-21 00:11:18 UTC
Update date2015-07-21 06:57:07 UTC
Primary IDFDB022271
Secondary Accession Numbers
  • FDB005599
Chemical Information
FooDB NameNeuraminic acid
DescriptionNeuraminic acids are the commonest sialic acids in nature. Most sialic acids on gangliosides share a core neuraminic acid (Neu) structure and are N-acylated at the C-5 position with either an N-acetyl or an N-glycolyl group (giving Neu5Ac or Neu5Gc, respectively). It was originally thought that unsubstituted glycosidically linked Neu did not occur in nature. However, there have been several reports suggesting its presence in gangliosides and more recently in mucin-type glycoproteins. The N- or O-substituted derivatives of neuraminic acid are collectively known as sialic acids, the predominant one being N-acetylneuraminic acid. The amino group bears either an acetyl or a glycolyl group. The hydroxyl substituents may vary considerably: acetyl, lactyl, methyl, sulfate and phosphate groups have been found. Sialic acids are found widely distributed in animal tissues. Sialic acid rich glycoproteins bind selectin in humans and other organisms. Cancer cells that can metastasize often have a lot of sialic acid rich glycoproteins. This helps these late stage cancer cells enter the blood stream. (PMID: 11884388) [HMDB]
CAS Number114-04-5
Structure
Thumb
Synonyms
SynonymSource
NeuraminateGenerator
5-(Acetylamino)-3,5-dideoxy-beta-L-erythro-2-nonulopyranosonateHMDB
5-(Acetylamino)-3,5-dideoxy-beta-L-erythro-2-nonulopyranosonic acidHMDB
O-SialateHMDB
O-Sialic acidHMDB
b-NeuraminateHMDB
b-Neuraminic acidHMDB
beta-NeuraminateHMDB
Β-neuraminateHMDB
Β-neuraminic acidHMDB
5-(acetylamino)-3,5-dideoxy-beta-L-erythro-2-nonulopyranosonatehmdb
5-(acetylamino)-3,5-dideoxy-beta-L-erythro-2-nonulopyranosonic acidhmdb
O-sialatehmdb
Predicted Properties
PropertyValueSource
Water Solubility255 g/LALOGPS
logP-3.3ALOGPS
logP-5.6ChemAxon
logS-0.02ALOGPS
pKa (Strongest Acidic)2.72ChemAxon
pKa (Strongest Basic)8.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area173.7 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.34 m³·mol⁻¹ChemAxon
Polarizability23.67 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H17NO8
IUPAC name(2S,4S,5R,6R)-5-amino-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
InChI IdentifierInChI=1S/C9H17NO8/c10-5-3(12)1-9(17,8(15)16)18-7(5)6(14)4(13)2-11/h3-7,11-14,17H,1-2,10H2,(H,15,16)/t3-,4+,5+,6+,7+,9-/m0/s1
InChI KeyCERZMXAJYMMUDR-YOQZMRDMSA-N
Isomeric SMILESN[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O
Average Molecular Weight267.2332
Monoisotopic Molecular Weight267.095416525
Classification
Description Belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl carnitines
Alternative Parents
Substituents
  • Acyl-carnitine
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSNeuraminic-acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-08i3-9120000000-3c41863dc43e1c340e0cSpectrum
Predicted GC-MSNeuraminic-acid, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dl-9050317000-14973db7ffcbfc34052eSpectrum
Predicted GC-MSNeuraminic-acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeuraminic-acid, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0090000000-d89dc6b36e86f946452e2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-9750000000-2aed2f62b96aad393b882016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9210000000-97dc8f0546cc39db37502016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0wna-5960000000-b190e5b95aab09e21fd32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9300000000-716acbc025a479fc33f72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-83bec5b63a8ab9d103cf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3190000000-f2d299e55cb15d9bd7f32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-9220000000-af4f3586fa7d7a2ccaf92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052o-9000000000-fbd3594b908b216886e62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-4868512633217955d5ba2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fur-3960000000-6a998b7b483922ea5dc82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0200-9400000000-eb39b86e7545b7da59f62021-09-22View Spectrum
NMRNot Available
ChemSpider ID447972
ChEMBL IDNot Available
KEGG Compound IDC06469
Pubchem Compound ID513472
Pubchem Substance IDNot Available
ChEBI ID27851
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00830
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNeuraminic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Bifunctional UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinaseGNEQ9Y223
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference